Mecillinam

Base Information

• Chemical Name: Mecillinam
• CAS No.: 32887-01-7
• Deprecated CAS: 51556-89-9,70178-27-7,73937-07-2,79580-20-4
• Molecular Formula: C₁₅H₂₃N₃O₃S
• Molecular Weight: 325.432
• European Community (EC) Number: 251-277-1
• UNII: V10579P3QZ
• DSSTox Substance ID: DTXSID3022584
• Nikkaji Number: J19.342I
• Wikipedia: Mecillinam
• Wikidata: Q13019044
• NCI Thesaurus Code: C65229
• Metabolomics Workbench ID: 57656
• ChEMBL ID: CHEMBL530,CHEMBL258646
• Mol file: 32887-01-7.mol

Synonyms:Amdinocillin;FL 1060;FL-1060;FL1060;Mecillinam;Penicillin Hx

Chemical Property of Mecillinam

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 156 °C
• Refractive Index: 1.686
• Boiling Point: 550.553 °C at 760 mmHg
• PKA: pKa 3.40 (Uncertain)
• Flash Point: 286.764 °C
• PSA: 98.51000
• Density: 1.447 g/cm³
• LogP: 1.28200
• Storage Temp.: Store at?0-5°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• Water Solubility.: Soluble in water at approximately 1mg/ml
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 325.14601278
• Heavy Atom Count: 22
• Complexity: 500

Purity/Quality:

98%,99%, ^*data from raw suppliers

Amdinocillin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(C2=O)N=CN3CCCCCC3)C(=O)O)C
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N=CN3CCCCCC3)C(=O)O)C
• Recent ClinicalTrials: Ibuprofen Versus Mecillinam for Uncomplicated Cystitis
• Recent EU Clinical Trials: Short course antibiotic treatment of Gram-negative bacteremia: A multicenter, randomized, non-blinded, non-inferiority interventional study
• Uses: Effective against Gram-negative bacteria Active antibacterial against gram-negative bacteria Mecillinam (amidinocillin) is a penicillin nucleus (6 APA) derivative, active in vitro against most aerobic and anaerobic Gram-negative bacilli, including E. coli and B. fraglis, but not active against Staphylococcus aureus, Enterococcus, or Pseudomonas. Mecillinam is synergistic with other beta-lactam drugs and therefore can be used in combination to treat severe Gram-negative infections. Although its in vitro efficacy is convincing, there are not enough clinical trials to support its use for intra-abdominal infections.
• Therapeutic Function: Antibacterial
• Clinical Use: Urinary tract infection (pivmecillinam) Other infections with susceptible Gram-negative bacilli (usually in combination with other agents)

Technology Process of Mecillinam

There total 5 articles about Mecillinam which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

6-Aminopenicillanic Acid (551-16-6) + N-formylhexamethyleneimine dimethylsulfate (65009-95-2) → mecillinam (32887-01-7,72312-33-5)

Guidance literature:

With triethylamine; In dichloromethane; 1.) 35 deg C, 30 min; 2.) 0-5 deg C, 1 h;

DOI:10.1248/cpb.35.642

Reference yield:

→ mecillinam (32887-01-7,72312-33-5)

Guidance literature:

Reference yield:

→ 6β-azepan-1-ylmethyleneamino-penicillanic acid (32887-01-7,72312-33-5)

Guidance literature:

6-Aminopenizillansaeuretrimethylsilylester, 1. /BRN= 163211/, CHCl3, 2. Triaethylamin, -70grad, 3. Erwaermen bis 0grad;

upstream raw materials:

6-Aminopenicillanic Acid

N-formylhexamethyleneimine dimethylsulfate

Downstream raw materials:

(4S)-2t-((R)-azepan-1-ylmethyleneamino-carboxy-methyl)-5,5-dimethyl-thiazolidine-4r-carboxylic acid

mecillinam (2-oxo-5-phenyl-1,3-dioxol-4-yl)methyl ester hydrochloride

Refernces

• 1、 Sakamoto,Ikeda,Hirayama,Moriyama,Sotomura,Tsukamoto. "Studies on prodrugs. VI. Preparation and characterization of (5-substituted 2-oxo-1,3-dioxol-4-yl)methyl esters of mecillinam". . p. 642 - 646. Retrieved 2007/10/02.